Things to do in Chicago

Jazz Festival, Bike the Drive and more: Things to do in Chicago this Labor Day weekend

Labor Day this year lands on Sept. 4, 2023

Labor Day weekend is near and many are planning how they plan to celebrate the long holiday weekend in Chicago, whether it be through big festivals, sporting events and more.

Labor Day this year lands on Sept. 4, 2023.

Here's a look at some ways to celebrate the long weekend:

North Coast Music Festival

The popular annual Labor Day weekend music festival at SeatGeek Stadium in Bridgeview will bring headliners like Marshmallow and Zeds Dead for the long weekend. The festival takes place from Sept. 1-3. Details here.

Jazz Festival

The Chicago Jazz Festival is the oldest of Chicago’s free lakefront music festivals, according to the city. The main shows will take place at Millennium Park, with a number of other performances scattered around Chicago neighborhoods. It runs from Aug. 31-Sept. 3 and admission is free. Details here.

Bike the Drive

The annual Bike the Drive event, which sees thousands of bike riders taking over the popular Lake Shore Drive over Labor Day weekend, is set to ride off on Sept. 3.

The event is a fundraiser for the Active Transportation Alliance. Registration and event information can be found here.

Neighborhood festivals in Chicago

A number of neighborhood festivals will also be held around the city for the holiday weekend.

According to Choose Chicago, the list includes the following:

  • WingOut Chicago: Sample a variety of award-winning wings and sauces in the heart of Wrigleyville, then vote for your favorites.
  • African Festival of the Arts: This culturally immersive event recreates an African village in Washington Park, with live music, yoga, dancing, vendors, and culinary delights.
  • Taste of Polonia Festival: Celebrate Chicago’s Polish heritage with live music, a casino, a beer garden, kids area, and of course, endless Polish food and beer.
  • West Loop Art Fest: Come browse four blocks of unique art across a range of mediums, plus live music and wine tastings.

Sporting events

Many of Chicago's beloved sports teams will be competing in the city for the holiday weekend, including both the Chicago Cubs and Chicago White Sox.

The Sox are set to play the Tigers at Guaranteed Rate Field from Sept. 1-3, while the Cubs will take on the Giants at Wrigley Field on Sept. 4.

There's also the Chicago Football Classic taking place on Sept. 2 at Soldier Field, featuring a contest between the Central State Marauders and Mississippi Valley State Delta Devils, and a Chicago Sky game against the New York Liberty on Sept. 3 at the Wintrust Arena.

Architecture Boat Tour

While the architecture boat cruises may be considered a tourist attraction for many, even locals say they enjoy it.

"As you're going up and down the Chicago River and on Lake Michigan, you're seeing the city’s evolving architecture, which is changing every year" said Andrew Sargis, director of sales and marketing for Wendella Tours and Cruises.

Whether you're taking the ride for the first time or the 50th, bringing out-of-town guests out for a memorable activity or just itching to be a tourist in your own city, here are some things to know about the Chicago Architecture Boat Tour.

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